Tributyl[fluoro(tributyl-lambda~5~-phosphanylidene)methyl]phosphanium chloride | 84195-43-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氟化物
• 英文名称: Tributyl[fluoro(tributyl-lambda~5~-phosphanylidene)methyl]phosphanium chloride
• 英文别名: tributyl-[fluoro-(tributyl-λ5-phosphanylidene)methyl]phosphanium;chloride
• CAS: 84195-43-7
• 化学式: C₂₅H₅₄FP₂*Cl
• 分子量: 471.103
• InChiKey: IKZAVIMRIJABDR-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  6.88
• 重原子数：
  29
• 可旋转键数：
  19
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Tributyl[fluoro(tributyl-lambda~5~-phosphanylidene)methyl]phosphanium chloride 在 氯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 tributyl-[dichloro(fluoro)methyl]phosphanium;chloride
  参考文献：
  名称：

  Fluorinated phosphoranium salts: syntheses and mechanisms of formation, hydrolysis, and halogenation

  摘要：

  DOI：

  10.1021/jo00237a026
• 作为产物：
  描述：

  一氟三氯甲烷 、 三丁基膦 以 二氯甲烷 为溶剂， 生成 Tributyl[fluoro(tributyl-lambda~5~-phosphanylidene)methyl]phosphanium chloride
  参考文献：
  名称：

  Monofluoro Analogs of Eugenol Methyl Ether as Novel Attractants for the Oriental Fruit Fly

  摘要：

  Monofluoro analogs of eugenol methyl ether as potential attractants for the Oriental fruit fly (Bactrocera dorsalis, Hendel) were synthesized using selective fluorination reactions: electrophilic hydro- and iodofluorination, fluorodehydroxylation with (diethylamido)sulfur trifluoride (DAST), and Wittig fluoroolefination through the stabilized ylides. Unusual reduction of the double bond was detected in a reaction of eugenol methyl ether with pyridinium poly(hydrogen fluoride). Bis-[(3,4-dimethoxyphenyl)alkyl] carbonates were identified as the novel nucleophilic substitution products of the intermediate generated from the reaction of 3,4-dimethoxybenzenealkanols with DAST. Reductive desulfonylation of fluorovinyl sulfone 24-(Z) with sodium amalgam afforded 1,2-dimethoxy-4-(3-fluoro-2-propenyl)benzene (E/Z = 85:15) which was highly attractive to the Oriental fruit fly.

  DOI：

  10.1021/jo00105a019

文献信息

• Regiospecific preparation of α,α-dihalofluoromethyl perfluoroalkyl ketones
  作者：In Howa Jeong、Donald J. Burton、Daryl G. Cox

  DOI：10.1016/s0040-4039(00)83859-9

  日期：1986.1

  Acylation of -phosphoranium salts with -acyl chlorides gives the corresponding -perfluoro betaine in high yield. Subsequent chlorination or bromination regiospecifically yields the α,α-dihalofluoromethyl perfluoroalkyl ketones.

  -磷鎓盐与-酰氯的酰化以高收率得到相应的-全氟甜菜碱。随后的氯化或溴化区域特异性地产生α，α-二卤代氟甲基全氟烷基酮。
• Alternative synthetic routes to hydrofluoroolefins
  作者：Yu. L. Yagupolskii、N.V. Pavlenko、S.V. Shelyazhenko、A.A. Filatov、M.M. Kremlev、A.I. Mushta、I.I. Gerus、Sheng Peng、V.A. Petrov、Mario Nappa

  DOI：10.1016/j.jfluchem.2015.08.001

  日期：2015.11

  A series of hydrofluoroolefins with -CF=CH2, -CH=CHF and -CH=CF2 groups were designed and prepared via various synthetic routes, including HX or BrF elimination, Wittig-type olefination or fluorination using SF4. (C) 2015 Elsevier B.V. All rights reserved.
• Regiospecific preparation of α,α-dihalofluoromethyl perfluoroalkyl ketones via halogenation of perfluoro betaines
  作者：Donald J. Burton、In Howa Jeong

  DOI：10.1016/s0022-1139(00)80099-8

  日期：1993.6

  Acylation of fluorinated phosphoranium salts with perfluorinated acyl chlorides provided the corresponding (Z)-perfluoro betaines in high yield. Subsequent chlorination or bromination of the betaines regiospecifically yields the alpha,alpha-dihalofluoromethyl perfluoroalkyl ketones. Halogen specificity is best controlled via use of CFCl3/Cl2 for the preparation of dichloroketones and CFBr3/Br2 for the corresponding dibromoketones. The dihalophosphorane by-product can promote a halogen-exchange reaction with ketones.
• Wittig olefination via reaction of fluorine-containing phosphoranium salts and F-acyl fluorides. A new approach to fluoroolefin synthesis
  作者：Donald J. Burton、Daryl G. Cox

  DOI：10.1021/ja00341a070

  日期：1983.2
• Monofluoro Analogs of Eugenol Methyl Ether as Novel Attractants for the Oriental Fruit Fly
  作者：Achot P. Khrimian、Albert B. DeMilo、Rolland M. Waters、Nicanor J. Liquido、Jesse M. Nicholson

  DOI：10.1021/jo00105a019

  日期：1994.12

  Monofluoro analogs of eugenol methyl ether as potential attractants for the Oriental fruit fly (Bactrocera dorsalis, Hendel) were synthesized using selective fluorination reactions: electrophilic hydro- and iodofluorination, fluorodehydroxylation with (diethylamido)sulfur trifluoride (DAST), and Wittig fluoroolefination through the stabilized ylides. Unusual reduction of the double bond was detected in a reaction of eugenol methyl ether with pyridinium poly(hydrogen fluoride). Bis-[(3,4-dimethoxyphenyl)alkyl] carbonates were identified as the novel nucleophilic substitution products of the intermediate generated from the reaction of 3,4-dimethoxybenzenealkanols with DAST. Reductive desulfonylation of fluorovinyl sulfone 24-(Z) with sodium amalgam afforded 1,2-dimethoxy-4-(3-fluoro-2-propenyl)benzene (E/Z = 85:15) which was highly attractive to the Oriental fruit fly.